PROBLEM 12.10
Question
Question: What is the structure of cis-jasmone, a natural product isolated from jasmine flowers, formed by the treatment of alkyne A with H2 in the presence of the Lindlar catalyst?
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Answer
Structure of cis-jasmone
Structure of Alkyne A
1Partial reduction of alkynes
The H2 - Palladium catalyst is very reactive on alkynes, and hence complete reduction of alkynes is made. To cease reaction of alkyne at alkene step, a less reactive Lindlar catalyst is used
2Reduction of alkynes to cis alkenes
The alkynes can be reduced to cis alkenes by using hydrogen on the Lindlar catalyst
3Synthesis of cis-jasmone
The reaction of alkyne A with on the Lindlar catalyst to produce cis-jasmone is represented as:
Synthesis of cis-jasmone from compound A (2-cyclopentanone)
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